Family-friendly vacation rentals in Berkshire County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Berkshire County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Loft in Great Barrington

4.99 out of 5 average rating, 296 reviews

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

Jul. 21 – 28

$278 CAD per night

Guest favourite

Chalet in Otis

4.94 out of 5 average rating, 351 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Jul. 19 – 26

$612 CAD per night

Guest favourite

Cottage in Lanesborough

4.93 out of 5 average rating, 220 reviews

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

Sep. 23 – 30

$296 CAD per night

Guest favourite

Guesthouse in Becket

4.93 out of 5 average rating, 258 reviews

Country Cabin

Lovely private country setting. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of the request.) The space is for 2 adults but I allow for flexibility, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.

Oct. 7 – 14

$189 CAD per night

Guest favourite

Home in Dalton

4.92 out of 5 average rating, 171 reviews

Brooksong, the perfect Berkshires getaway

Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!

Sep. 27 – Oct. 4

$605 CAD per night

Guest favourite

Guest suite in South Lee

4.92 out of 5 average rating, 190 reviews

Sunny Riverside Apartment

The Berkshires are a perfect spot for a getaway week or weekend. You will enjoy this cozy 2-story apartment, easily accessible to all that the region has to offer. The apartment has a fully equipped kitchen, dining space, living area, and two bedrooms, overlooking the Housatonic River. Every town in South County is 5-15 minutes drive, and in 50 minutes you could be at The Clark Museum or Mass MOCA in North County. Several ski areas are nearby, and Kripalu is just an easy 10 minute drive.

Apr. 10 – 17

$197 CAD per night

Guest favourite

Home in Chester

4.96 out of 5 average rating, 311 reviews

Riverfront Getaway

Our place is on a gentle flowing river, close to waterfalls, walks and the Berkshire cultural sites like Tanglewood and Jacobs Pillow . You’ll love our place because of the river, the deck, the hot tub; complete tranquility and a home away from home. Close to some great sites and activities, far enough away to escape. Our place is good for couples, friends and solo adventurers. Snowboarders/Skiers (or snow bunnies) and families can have great fun too! Sit back, relax and enjoy our home!

Oct. 14 – 21

$294 CAD per night

Guest favourite

Apartment in Great Barrington

4.93 out of 5 average rating, 179 reviews

Secluded but not isolated Berkshire Retreat

1.5 bedroom 1.5 bath self contained apartment (apprx. 950 sq ft ) attached to the main house set on a secluded 5.5 acre lot 2.9 miles from downtown Great Barrington . There is a CB2 day bed in the living room that sleeps an additional 2 people comfortably. Extra charge of $25/night +tax if the extra bedroom is used in 2 person reservations. $20 extra cleaning fee for reservations of 4 or more. During heating season not suitable for children under 5 because of pellet stove. .

Sep. 12 – 19

$320 CAD per night

Guest favourite

Guesthouse in New Marlborough

4.91 out of 5 average rating, 180 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

Nov. 16 – 23

$261 CAD per night

Guest favourite

Apartment in Sandisfield

4.92 out of 5 average rating, 227 reviews

Sunny Berkshire Studio Apartment

Sunny many windowed studio apartment attached at west end of the main house. Self contained with kitchen and bathroom. Plus addition sleeping area (attached bedroom). Studio and bedroom have full size beds Studio also has narrow twin futon. 1 mile long gravel road for a "walk out the door and go" wake up morning hike. State forest is across from house, along Bosworth Road and along Rt 57. Long Term Guests welcome. $5/guest after 2. PET FEE: $25/stay

Dec. 20 – 27

$173 CAD per night

Guest favourite

Barn in Williamstown

4.97 out of 5 average rating, 261 reviews

Cozy barn apartment on the river

Private converted first floor barn apartment in a New England home next to the Green River. Comfortable with unique furnishings and back door to river patio. Sleeps 1-2 comfortably. Can accommodate 4 with the extra sleeper tri-fold mattress, (Best for 1-2 smaller children). Private full bath. Great for 1-2 adults or a family with smaller children. Due to Coronavirus we are doing extensive disinfecting and allowing for 72 hours between bookings.

Jan. 17 – 24

$230 CAD per night

Guest favourite

Home in New Lebanon

4.99 out of 5 average rating, 348 reviews

The old sawmill from 1771

The oldest house in town, fully renovated. Beautiful two-story living room with leafy, private back deck for meals outside. Kitchen with stone counters, gas cook top, and dishwasher; two bathrooms with warm floors. Floorboards upstairs a foot wide; queen size bed with view over the trees, creek and porch.

Nov. 16 – 23

$211 CAD per night